CN102675092A - Method for preparing 2-aryl-2,2-dimethyl methyl acetate - Google Patents
Method for preparing 2-aryl-2,2-dimethyl methyl acetate Download PDFInfo
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- CN102675092A CN102675092A CN2011100605975A CN201110060597A CN102675092A CN 102675092 A CN102675092 A CN 102675092A CN 2011100605975 A CN2011100605975 A CN 2011100605975A CN 201110060597 A CN201110060597 A CN 201110060597A CN 102675092 A CN102675092 A CN 102675092A
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- aryl
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- salt
- sylvite
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- 238000000034 method Methods 0.000 title claims abstract description 33
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 75
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 25
- 239000012312 sodium hydride Substances 0.000 claims abstract description 25
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 15
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000011777 magnesium Substances 0.000 claims abstract description 4
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 4
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 58
- 239000005457 ice water Substances 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 27
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 24
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 17
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 14
- 159000000013 aluminium salts Chemical class 0.000 claims description 14
- 229910000329 aluminium sulfate Inorganic materials 0.000 claims description 14
- 159000000003 magnesium salts Chemical class 0.000 claims description 14
- 239000001103 potassium chloride Substances 0.000 claims description 14
- 235000011164 potassium chloride Nutrition 0.000 claims description 14
- -1 methoxyl group Chemical group 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 abstract description 4
- 238000005886 esterification reaction Methods 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- 229960003424 phenylacetic acid Drugs 0.000 abstract 2
- 239000003279 phenylacetic acid Substances 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 238000011403 purification operation Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000010438 heat treatment Methods 0.000 description 31
- 238000012544 monitoring process Methods 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 238000009835 boiling Methods 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- 238000003810 ethyl acetate extraction Methods 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 235000002639 sodium chloride Nutrition 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 8
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- WMUZDBZPDLHUMW-UHFFFAOYSA-N (2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1[N+]([O-])=O WMUZDBZPDLHUMW-UHFFFAOYSA-N 0.000 description 2
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 2
- 0 C*c1cc(*)c(C*)c(C2C3C2C3)c1C Chemical compound C*c1cc(*)c(C*)c(C2C3C2C3)c1C 0.000 description 2
- 101150042817 NFS1 gene Proteins 0.000 description 2
- 101100126298 Rickettsia conorii (strain ATCC VR-613 / Malish 7) iscS gene Proteins 0.000 description 2
- 101150114492 SPL1 gene Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JYACVTTYKZGWLQ-UHFFFAOYSA-N methyl 2-(2-bromophenyl)-2-methylpropanoate Chemical class COC(=O)C(C)(C)C1=CC=CC=C1Br JYACVTTYKZGWLQ-UHFFFAOYSA-N 0.000 description 2
- VUNAVDASMZBUSC-UHFFFAOYSA-N methyl 2-(4-methoxyphenyl)-2-methylpropanoate Chemical class COC(=O)C(C)(C)C1=CC=C(OC)C=C1 VUNAVDASMZBUSC-UHFFFAOYSA-N 0.000 description 2
- WITYUUTUSPKOAB-UHFFFAOYSA-N methyl 2-methyl-2-phenylpropanoate Chemical class COC(=O)C(C)(C)C1=CC=CC=C1 WITYUUTUSPKOAB-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GUAIAAXDEJZRBP-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=C(F)C=CC=C1Cl GUAIAAXDEJZRBP-UHFFFAOYSA-N 0.000 description 1
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZTBCOZQPDZZCJO-UHFFFAOYSA-N methyl 2-(3-bromophenyl)-2-methylpropanoate Chemical class COC(=O)C(C)(C)C1=CC=CC(Br)=C1 ZTBCOZQPDZZCJO-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940006198 sodium phenylacetate Drugs 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN201110060597.5A CN102675092B (en) | 2011-03-14 | 2011-03-14 | Method for preparing 2-aryl-2,2-dimethyl methyl acetate |
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CN201110060597.5A CN102675092B (en) | 2011-03-14 | 2011-03-14 | Method for preparing 2-aryl-2,2-dimethyl methyl acetate |
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CN102675092B CN102675092B (en) | 2014-11-05 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111072476A (en) * | 2019-12-06 | 2020-04-28 | 南京理工大学 | β -ketoester compound oxygen high-selectivity monofluoromethylation method |
CN111269083A (en) * | 2020-02-24 | 2020-06-12 | 珠海市柏瑞医药科技有限公司 | Synthesis method of Guerbet acid |
CN113121341A (en) * | 2019-12-31 | 2021-07-16 | 江苏中旗科技股份有限公司 | Method for synthesizing 2, 6-diethyl-4-methyl phenylacetate |
Citations (6)
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US20040146941A1 (en) * | 2002-11-04 | 2004-07-29 | Biliang Zhang | Chemical encoding technology for combinatorial synthesis |
CN1750820A (en) * | 2003-02-24 | 2006-03-22 | 沃纳-兰伯特公司 | Thiazole and oxazole derivatives which modulate PPAR activity |
CN1780821A (en) * | 2003-02-27 | 2006-05-31 | 艾博特公司 | Heterocyclic kinase inhibitors. |
CN101362678A (en) * | 2008-09-18 | 2009-02-11 | 南昌航空大学 | Methylation reaction |
WO2009039127A1 (en) * | 2007-09-17 | 2009-03-26 | Abbott Laboratories | Uracil or thymine derivative for treating hepatitis c |
CN101842360A (en) * | 2007-09-17 | 2010-09-22 | 雅培制药有限公司 | Anti-infective pyrimidines and uses thereof |
-
2011
- 2011-03-14 CN CN201110060597.5A patent/CN102675092B/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040146941A1 (en) * | 2002-11-04 | 2004-07-29 | Biliang Zhang | Chemical encoding technology for combinatorial synthesis |
CN1750820A (en) * | 2003-02-24 | 2006-03-22 | 沃纳-兰伯特公司 | Thiazole and oxazole derivatives which modulate PPAR activity |
CN1780821A (en) * | 2003-02-27 | 2006-05-31 | 艾博特公司 | Heterocyclic kinase inhibitors. |
WO2009039127A1 (en) * | 2007-09-17 | 2009-03-26 | Abbott Laboratories | Uracil or thymine derivative for treating hepatitis c |
CN101842360A (en) * | 2007-09-17 | 2010-09-22 | 雅培制药有限公司 | Anti-infective pyrimidines and uses thereof |
CN101362678A (en) * | 2008-09-18 | 2009-02-11 | 南昌航空大学 | Methylation reaction |
Non-Patent Citations (1)
Title |
---|
ARTHUR GOMTSYAN ET AL.: "Identification of (R)-1-(5-tert-Butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H-indazol-4-yl)urea(ABT-102) as a potent TRPV1 Antagonist for Pain Management", 《J.MED.CHEM.》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111072476A (en) * | 2019-12-06 | 2020-04-28 | 南京理工大学 | β -ketoester compound oxygen high-selectivity monofluoromethylation method |
CN111072476B (en) * | 2019-12-06 | 2022-10-21 | 南京理工大学 | Method for high-selectivity fluoromethylation of beta-keto ester compounds on oxygen |
CN113121341A (en) * | 2019-12-31 | 2021-07-16 | 江苏中旗科技股份有限公司 | Method for synthesizing 2, 6-diethyl-4-methyl phenylacetate |
CN111269083A (en) * | 2020-02-24 | 2020-06-12 | 珠海市柏瑞医药科技有限公司 | Synthesis method of Guerbet acid |
CN111269083B (en) * | 2020-02-24 | 2023-08-25 | 珠海市柏瑞医药科技有限公司 | Synthesis method of guerbet acid |
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CN102675092B (en) | 2014-11-05 |
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Owner name: JIANGSU ZHONGDAN CHEMICAL ENGINEERING TECHNOLOGY C Free format text: FORMER OWNER: JIANGSU ZHONGDAN PHARMACEUTICAL RESEARCH COMPANY LIMITED Effective date: 20150618 Free format text: FORMER OWNER: JIANGSU ZHONGDAN CHEMICAL ENGINEERING TECHNOLOGY CO., LTD. Effective date: 20150618 |
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Effective date of registration: 20150618 Address after: 225453, No. 8, Tongjiang Road, Yanjiang Economic Development Zone, Taixing, Jiangsu, Taizhou Patentee after: JIANGSU ZHONGDAN CHEMICAL TECHNOLOGY Co.,Ltd. Address before: 210009 science and technology innovation building, 5 new exemplary Road, Nanjing, Jiangsu B-25 Patentee before: JIANGSU ZHONGDAN PHARMACEUTICAL RESEARCH Co.,Ltd. Patentee before: JIANGSU ZHONGDAN CHEMICAL TECHNOLOGY Co.,Ltd. |
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Denomination of invention: A method for preparing 2-aryl-2,2-dimethylacetate methyl ester Granted publication date: 20141105 Pledgee: Industrial Bank Co.,Ltd. Taizhou Branch Pledgor: JIANGSU ZHONGDAN CHEMICAL TECHNOLOGY Co.,Ltd. Registration number: Y2024980013262 |